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Accession:CHEBI:74921 term browser browse the term
Definition:A peptide and carboxamide that is L-leucyl-L-phenylalaninamide, L-Leu-L-Phe-NH2, which has been acylated on the N-terminus by a Phe-Phe hydroxyethylene dipeptide isotere, 2R-benzyl-5S-tert-butoxycarbonylamino-4R-hydroxy-6-phenylhexanoic acid. Compounds based on the structure of L-685,458 are potent inhibitors of gamma-secretase, which mediates the final catalytic step that generates the amyloid beta-peptide (Abeta), which assembles into the neurotoxic aggregates in the brains of sufferers of Alzheimer's disease.
Synonyms:exact_synonym: N-{(2R,4R,5S)-2-benzyl-5-[(tert-butoxycarbonyl)amino]-4-hydroxy-6-phenylhexanoyl}-L-leucyl-L-phenylalaninamide
 related_synonym: (1S,2R,4R)-{1-benzyl-4-[1-(1S)-carbamoyl-(2-phenylethylcarbamoyl)-(1S)-3-methylbutylcarbamoyl]-2-hydroxy-5-phenylpentyl}carbamic acid tert-butyl ester;   (5S)-[tert-butoxycarbonylamino-6-phenyl-(4R)-hydroxy-(2R)-benzylhexanoyl]-L-Leu-L-Phe-NH2;   Formula=C39H52N4O6;   InChI=1S/C39H52N4O6/c1-26(2)21-33(37(47)41-32(35(40)45)24-29-19-13-8-14-20-29)42-36(46)30(22-27-15-9-6-10-16-27)25-34(44)31(23-28-17-11-7-12-18-28)43-38(48)49-39(3,4)5/h6-20,26,30-34,44H,21-25H2,1-5H3,(H2,40,45)(H,41,47)(H,42,46)(H,43,48)/t30-,31+,32+,33+,34-/m1/s1;   InChIKey=MURCDOXDAHPNRQ-ZJKZPDEISA-N;   L-685458;   SMILES=CC(C)C[C@H](NC(=O)[C@@H](C[C@@H](O)[C@H](Cc1ccccc1)NC(=O)OC(C)(C)C)Cc1ccccc1)C(=O)N[C@@H](Cc1ccccc1)C(N)=O;   {(1S)-benzyl-(4R)-[1-((1S)-carbamoyl-2-phenyl-ethylcarbamoyl)-(1S)-3-methyl-butyl-carbamoyl]-(2R)-hydroxy-5-phenyl-pentyl} carbamic acid tert-butyl ester;   {1(S)-benzyl-4(R)-[1-(1(S)-carbamoyl-2-phenylethylcarbamoyl)-1(S)-3-methyl-butylcarbamoyl]-2(R)-hydroxy-5-phenylpentyl}carbamic acid tert-butyl ester
 xref: PMID:10801983 "Europe PMC";   PMID:10864326 "Europe PMC";   PMID:10913280 "Europe PMC";   Reaxys:8816919 "Reaxys"

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  CHEBI ontology 19669
    role 19613
      application 19235
        protecting group 0
          tert-butoxycarbonyl group 0
            L-685,458 0
              GCB 0
Path 2
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  CHEBI ontology 19669
    subatomic particle 19665
      composite particle 19665
        hadron 19665
          baryon 19665
            nucleon 19665
              atomic nucleus 19665
                atom 19665
                  main group element atom 19545
                    p-block element atom 19545
                      carbon group element atom 19428
                        carbon atom 19420
                          organic molecular entity 19420
                            organic group 18343
                              organic divalent group 18334
                                organodiyl group 18334
                                  carbonyl group 18222
                                    carbonyl compound 18222
                                      carboxylic acid 17923
                                        carboacyl group 16943
                                          univalent carboacyl group 16943
                                            carbamoyl group 16622
                                              carboxamide 16622
                                                peptide 9297
                                                  L-685,458 0
                                                    GCB 0
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RGD is funded by grant HL64541 from the National Heart, Lung, and Blood Institute on behalf of the NIH.